Reactions of Amino-Substituted Cyclodextrins with 2-Arylpropanoic Acid Derivatives

Abstract

Reactions of 6^A-amino-6^A-deoxy-β-cyclodextrin and 3^A-amino-3^A-deoxy-(2^AS,3^AS)-β-cyclodextrin with the 3-nitrophenyl esters of 2-phenylpropanoic acid and Ibuprofen occur with only low diastereoselectivity, to afford the corresponding arylpropanamido-substituted cyclodextrins. These amides are also formed by decarboxylation of corresponding malonates, again with only low diastereoselectivity. The n.m.r. spectra of the amido-substituted cyclodextrins indicate that the aryl substituent is included within the cyclodextrin annulus at low temperature, but becomes dissociated from the cavity as the temperature is increased.